Lasting Impressions
I still remember the first time a friend of a friend showed me his cock during a game of strip poker after school. I remember my first time, during a sleepover, that I sucked my friend's cock and he sucked mine. I remember the first time trying anal, as a bottom, how painfully awkward it was and how I wanted more.....even after I cried to stop after penetration and just a few strokes inside me. I remember going bareback for the first time with a guy I only knew for about three hours.....and it turning into an on/off again relationship for the next six years. It's funny how you replay those memories in your mind and they seem to get more erotic the more you replay them. For every amazing memory there are those that you wish you could forget or at least everyone that knew about those most embarrassing moments. Well, I am going to share with you one of the most embarrassing moments......
I was a mouthy, slightly full of myself thirteen year old. It's ironic since I was just this skinny, pale, weakling, with long shoulder length white blonde hair, blue eyes, I was the second shortest guy in my class with a small little cock. I was average looking or even a bit below in the looks department. I was full of myself around my friends but in public.... I was quiet and shy when not around them. I only had a few friends, so I was usually on my own. I thought I knew it all and had this overpowering conscience that never let me do anything too bad. I liked girls but girls didn't like me. My first sleepover in middle school had me sucking my friends cock and nearly choking to death on his foul tasting sperm. I had the smell of it in my nose for days after. The next sleepover, I let my friend stick his cock in my ass. It didn't go well ....... especially when once he broke through he buried it deep into my ass. I cried out so loud that his mom ran to the basement to see what was wrong. She had caught her son on top of me as he made two more plunges into me. My legs were kicking, I was red faced and balling my eyes out as she cried out in horror as to what she had witnessed. Needless to say, I was blamed as the bad influence even though it was his idea. I was driven home and grounded for a month. I never got to hang out with him again...or at least that's what our parents thought...
A mutual friend had invited us,along with several others, to a huge overnight sleepover. This friend happened to lived in town but close to the sculpture park. What made this sculpture park unique was that it had one piece of art that happened to have these "tentacles" that were in similar shape to the male anatomy. It had been a rumor that the artist was gay since he had never married even though he was considered attractive. It was also rumored that our super sexy seventh grade teacher was having an affair with the principal and one of our friends witnessed them having sex on her desk. This same friend confessed he had sex with a senior .....so you get the point....he was just full of shit like the rest of us.
The party started out with racing go carts in his backyard. We played some games, ate pizza, drank pop, and then watched him open gifts. After that we had cake and ice cream. We did some more go carts. Then we played hide and seek around the neighborhood when it got dark. My friend, Jeff, who I had sucked his cock and had my first anal with was hiding with me down in a small creek. As we hid there, I got this funny feeling in my shorts when he brushed up against me. Jeff stared at me and somehow he just knew by my wide eyed expression. He told me to follow him. It's funny how you know that I probably shouldn't but I did anyway. We ran away from the party and made it to a gas station. There Jeff asked for the key to the bathroom located on the side of the station. He was granted the key and we went inside the one stall bathroom. There was a condom machine and Jeff bought two condoms with topless women on the packaging. He held out one for me. I reached for it but he took it away. He unzipped his jeans and pulled down his underwear. His long slender cock sprang upwards. He then yanked my shorts down with my underwear. My tiny little prick was instantly hardened. I stepped out of my shorts. Jeff had me lean up against the sink. He took the condom out. He carefully unfolded the packaging and took his spit his gum on the backside and slapped it on the mirror in front of me. Jeff knew I liked looking at naked breasts from the porn magazines he had under his mattress. I felt him rub his hard cock up between my tight pale ass cheeks. I started playing with myself. He put the condom on and was now pressing his tip on my tightly sealed hole. I think I was wanting it but the fear of the incoming pain was making my hole tight. I resisted as much as I could while Jeff continued to position himself. He burst into me. I let out a honking exhale as if all the air in my lungs had been forced out of me instantly. Surprisingly, it wasn't as bad as I expected. Yes, it felt awkward and yes it hurt a little but not as much as I had initially imagined. Jeff worked much slower this time. I was able to catch my breath as he worked in. He had one hand on his long shaft and one on my boney hip. His breathing was hard as he tried to go in further. I took long deep breaths and relaxed as much as I could. Still my ass was firmly clenched. Once Jeff got a rhythm going, he grabbed both my hips tightly. The long strokes were challenging as he stuffed my ass. My legs were shaky. I looked at Jeff through the mirror and he said to focus on the tits. Once I did that, I was transported into a fantasy of this it what it must feel like for her to have a cock inside. For a few moments, I didn't feel anything as Jeff was now fully inserted and the strokes were speeding up. His flesh slapping up against my tiny innocent ass echoed in the small one stall bathroom. The pain in my ass was increasing at an exponential rate. A sweat broke out all over my body. I was having a hard time breathing. I yanked my shirt off and threw it on the floor. Jeff was grunting hard as he pounded faster and faster. The pain was now feeling like a burning sensation inside me. My hands clasped over Jeff's that were locked into my hips. I began crying out to stop between the slapping sound. "Please hurry! I don't know how much more I can take!" Tears streamed down my face my vision got blurry and could not longer focus on the topless woman. My body was going numb, I was losing feeling in my ass and my legs were giving out. Jeff let out a joyous cry as he expunged his seeds. One jerk, two, then three..... Jeff withdrew his long sword out of my ass sheath. I grabbed the sink but could only hold on it for almost a minute before slumping to the floor. Jeff, in slight disgust, carefully removed the stinky, poop covered latex off his withering cock and with two fingers discarded it into the trash can. I admit the smell was not pleasant. I felt something oozing out of my weary ass and quickly plopped on the throne. The sounds of juicy farts echoed loudly. Contents were extracted and I tried to push out as much as I could. I felt backed up and a little sick as my ass was pulsating uncontrollably. Jeff left me to finish up and he returned the key. I sat there my legs were still shaky and I wondered how I was even going to be able to stand up. Not sure how long it took, but eventually I did get dressed and took the picture off the mirror and carefully removed the gum before sliding it in my back pocket. I walked gingerly with Jeff who kept and odd distance away from me.
In that short moment, I felt close to Jeff but once he had finished.....he seemed to be done with me. I felt a little hurt and let unseen tears flow for a brief time. We walked in silence and I felt ashamed. I wanted to say something but there wasn't anything as images of what just took place were replaying in my head. I sulked behind Jeff. He seemed a little put off my 'pussy-like" attitude. "Are you going to be like this when we get back to the party?" Jeff said exasperated.
I had no words, still in shock. We just looked at each other stopped on the sidewalk. Then Jeff started to crack a smile. I don't know why, but I did as well. We both started laughing. Jeff walked over to me and put an arm around my shoulder. "I've got an idea." He steered me away from the direction we were going.... I helplessly went.
We arrive at the sculpture park, it was dark except for a few working street lights. Jeff had guided me over to the one sculpture with the tentacles with rounded tips. Jeff took out his last condom. My ass was still pulsating and I could still feel Jeff's cock inside my hole. I told him there was no way. Jeff smiled shaking his head. "No dude, I want you to get fucked by this sculpture." I looked at the sculpture and then at Jeff.
"No way!" I wasn't going to do that. Jeff then told me things that sounded perfect to me. He seduced me right on the spot. He had taken the condom out and slipped it over one of the tentacles that was arched upwards about waist high on me. I slipped off my shorts and underwear kicking them away. I took my shirt off per Jeff's request. I then tried to mount it but it was too high. I needed help. Jeff got on all fours and I stepped up. I used one hand to guide me down. The tip felt cold and metallic. I used my other hand to counter balance. I was so shaky! I was looking all around if anyone was watching nervously. I bent my knees and that seemed to work as the tip entered me. It was much wider than I had anticipated. I quickly jumped up and off Jeff. I was gathering my clothes. Jeff stayed on all fours and encouraged me to go for it. He complimented me even more and explained how this would be burned into his brain forever. I got back up and lowered myself down onto the top. This time I went for it, since I only had to do it for a full minute then I could get off. I pushed down on the top and no longer needed Jeff's unstable back for support. I had to stand with my ass pushed outwards on my tippy toes. Jeff encouraged me to go down. I tried but the rigid dick inside my ass was unconforming. In order not to have my ass be ripped apart, I froze. I was sweating just staying on my toes to prevent the inevitable pain train coming my way. I tried to get off on my own but my toes were failing. I slipped down and now was in a prostate position. I begged Jeff but he just stood there until we heard a car. Fear coursed through my, intensed up, pain flooded in as my initial reaction to squat was a very poor choice. Jeff hid behind a bench as the car with it's lights streaked past. I had gone down on the tentacle and was gingerly trying to right myself. I grunted and cried simultaneously. I swore begged Jeff who was in shock at what he was witnessing. I kept trying to get off the metallic monstrosity but it held me fast. I tried a feeble jump.....Big Mistake!! It was like a mean fist being jammed up inside you all the way up your throat. The sensation of every nerve firing off at once and then the shock of being stuck and not in control made me puke. I threw up and Jeff who was watching my plight began to dry heave. I no longer felt anything as my stomach pushed out everything it had my weak legs were quaking and I continued to slide further down. I was convulsing violently and didn't notice the blue and red lights flashing. Jeff bolted. All I could do was cry out for help. I was lifted off the sculpture by two cops. I was then taken to the ER.
I was considered "Lucky!" No permanent internal damage was done. I wasn't charged because it was a small town and I was a very stupid teenager. Jeff later confessed that I had taken probably twelve inches at least. I didn't have a shit for two days after that.
Years later, I became very popular.....with guys :)
I was a mouthy, slightly full of myself thirteen year old. It's ironic since I was just this skinny, pale, weakling, with long shoulder length white blonde hair, blue eyes, I was the second shortest guy in my class with a small little cock. I was average looking or even a bit below in the looks department. I was full of myself around my friends but in public.... I was quiet and shy when not around them. I only had a few friends, so I was usually on my own. I thought I knew it all and had this overpowering conscience that never let me do anything too bad. I liked girls but girls didn't like me. My first sleepover in middle school had me sucking my friends cock and nearly choking to death on his foul tasting sperm. I had the smell of it in my nose for days after. The next sleepover, I let my friend stick his cock in my ass. It didn't go well ....... especially when once he broke through he buried it deep into my ass. I cried out so loud that his mom ran to the basement to see what was wrong. She had caught her son on top of me as he made two more plunges into me. My legs were kicking, I was red faced and balling my eyes out as she cried out in horror as to what she had witnessed. Needless to say, I was blamed as the bad influence even though it was his idea. I was driven home and grounded for a month. I never got to hang out with him again...or at least that's what our parents thought...
A mutual friend had invited us,along with several others, to a huge overnight sleepover. This friend happened to lived in town but close to the sculpture park. What made this sculpture park unique was that it had one piece of art that happened to have these "tentacles" that were in similar shape to the male anatomy. It had been a rumor that the artist was gay since he had never married even though he was considered attractive. It was also rumored that our super sexy seventh grade teacher was having an affair with the principal and one of our friends witnessed them having sex on her desk. This same friend confessed he had sex with a senior .....so you get the point....he was just full of shit like the rest of us.
The party started out with racing go carts in his backyard. We played some games, ate pizza, drank pop, and then watched him open gifts. After that we had cake and ice cream. We did some more go carts. Then we played hide and seek around the neighborhood when it got dark. My friend, Jeff, who I had sucked his cock and had my first anal with was hiding with me down in a small creek. As we hid there, I got this funny feeling in my shorts when he brushed up against me. Jeff stared at me and somehow he just knew by my wide eyed expression. He told me to follow him. It's funny how you know that I probably shouldn't but I did anyway. We ran away from the party and made it to a gas station. There Jeff asked for the key to the bathroom located on the side of the station. He was granted the key and we went inside the one stall bathroom. There was a condom machine and Jeff bought two condoms with topless women on the packaging. He held out one for me. I reached for it but he took it away. He unzipped his jeans and pulled down his underwear. His long slender cock sprang upwards. He then yanked my shorts down with my underwear. My tiny little prick was instantly hardened. I stepped out of my shorts. Jeff had me lean up against the sink. He took the condom out. He carefully unfolded the packaging and took his spit his gum on the backside and slapped it on the mirror in front of me. Jeff knew I liked looking at naked breasts from the porn magazines he had under his mattress. I felt him rub his hard cock up between my tight pale ass cheeks. I started playing with myself. He put the condom on and was now pressing his tip on my tightly sealed hole. I think I was wanting it but the fear of the incoming pain was making my hole tight. I resisted as much as I could while Jeff continued to position himself. He burst into me. I let out a honking exhale as if all the air in my lungs had been forced out of me instantly. Surprisingly, it wasn't as bad as I expected. Yes, it felt awkward and yes it hurt a little but not as much as I had initially imagined. Jeff worked much slower this time. I was able to catch my breath as he worked in. He had one hand on his long shaft and one on my boney hip. His breathing was hard as he tried to go in further. I took long deep breaths and relaxed as much as I could. Still my ass was firmly clenched. Once Jeff got a rhythm going, he grabbed both my hips tightly. The long strokes were challenging as he stuffed my ass. My legs were shaky. I looked at Jeff through the mirror and he said to focus on the tits. Once I did that, I was transported into a fantasy of this it what it must feel like for her to have a cock inside. For a few moments, I didn't feel anything as Jeff was now fully inserted and the strokes were speeding up. His flesh slapping up against my tiny innocent ass echoed in the small one stall bathroom. The pain in my ass was increasing at an exponential rate. A sweat broke out all over my body. I was having a hard time breathing. I yanked my shirt off and threw it on the floor. Jeff was grunting hard as he pounded faster and faster. The pain was now feeling like a burning sensation inside me. My hands clasped over Jeff's that were locked into my hips. I began crying out to stop between the slapping sound. "Please hurry! I don't know how much more I can take!" Tears streamed down my face my vision got blurry and could not longer focus on the topless woman. My body was going numb, I was losing feeling in my ass and my legs were giving out. Jeff let out a joyous cry as he expunged his seeds. One jerk, two, then three..... Jeff withdrew his long sword out of my ass sheath. I grabbed the sink but could only hold on it for almost a minute before slumping to the floor. Jeff, in slight disgust, carefully removed the stinky, poop covered latex off his withering cock and with two fingers discarded it into the trash can. I admit the smell was not pleasant. I felt something oozing out of my weary ass and quickly plopped on the throne. The sounds of juicy farts echoed loudly. Contents were extracted and I tried to push out as much as I could. I felt backed up and a little sick as my ass was pulsating uncontrollably. Jeff left me to finish up and he returned the key. I sat there my legs were still shaky and I wondered how I was even going to be able to stand up. Not sure how long it took, but eventually I did get dressed and took the picture off the mirror and carefully removed the gum before sliding it in my back pocket. I walked gingerly with Jeff who kept and odd distance away from me.
In that short moment, I felt close to Jeff but once he had finished.....he seemed to be done with me. I felt a little hurt and let unseen tears flow for a brief time. We walked in silence and I felt ashamed. I wanted to say something but there wasn't anything as images of what just took place were replaying in my head. I sulked behind Jeff. He seemed a little put off my 'pussy-like" attitude. "Are you going to be like this when we get back to the party?" Jeff said exasperated.
I had no words, still in shock. We just looked at each other stopped on the sidewalk. Then Jeff started to crack a smile. I don't know why, but I did as well. We both started laughing. Jeff walked over to me and put an arm around my shoulder. "I've got an idea." He steered me away from the direction we were going.... I helplessly went.
We arrive at the sculpture park, it was dark except for a few working street lights. Jeff had guided me over to the one sculpture with the tentacles with rounded tips. Jeff took out his last condom. My ass was still pulsating and I could still feel Jeff's cock inside my hole. I told him there was no way. Jeff smiled shaking his head. "No dude, I want you to get fucked by this sculpture." I looked at the sculpture and then at Jeff.
"No way!" I wasn't going to do that. Jeff then told me things that sounded perfect to me. He seduced me right on the spot. He had taken the condom out and slipped it over one of the tentacles that was arched upwards about waist high on me. I slipped off my shorts and underwear kicking them away. I took my shirt off per Jeff's request. I then tried to mount it but it was too high. I needed help. Jeff got on all fours and I stepped up. I used one hand to guide me down. The tip felt cold and metallic. I used my other hand to counter balance. I was so shaky! I was looking all around if anyone was watching nervously. I bent my knees and that seemed to work as the tip entered me. It was much wider than I had anticipated. I quickly jumped up and off Jeff. I was gathering my clothes. Jeff stayed on all fours and encouraged me to go for it. He complimented me even more and explained how this would be burned into his brain forever. I got back up and lowered myself down onto the top. This time I went for it, since I only had to do it for a full minute then I could get off. I pushed down on the top and no longer needed Jeff's unstable back for support. I had to stand with my ass pushed outwards on my tippy toes. Jeff encouraged me to go down. I tried but the rigid dick inside my ass was unconforming. In order not to have my ass be ripped apart, I froze. I was sweating just staying on my toes to prevent the inevitable pain train coming my way. I tried to get off on my own but my toes were failing. I slipped down and now was in a prostate position. I begged Jeff but he just stood there until we heard a car. Fear coursed through my, intensed up, pain flooded in as my initial reaction to squat was a very poor choice. Jeff hid behind a bench as the car with it's lights streaked past. I had gone down on the tentacle and was gingerly trying to right myself. I grunted and cried simultaneously. I swore begged Jeff who was in shock at what he was witnessing. I kept trying to get off the metallic monstrosity but it held me fast. I tried a feeble jump.....Big Mistake!! It was like a mean fist being jammed up inside you all the way up your throat. The sensation of every nerve firing off at once and then the shock of being stuck and not in control made me puke. I threw up and Jeff who was watching my plight began to dry heave. I no longer felt anything as my stomach pushed out everything it had my weak legs were quaking and I continued to slide further down. I was convulsing violently and didn't notice the blue and red lights flashing. Jeff bolted. All I could do was cry out for help. I was lifted off the sculpture by two cops. I was then taken to the ER.
I was considered "Lucky!" No permanent internal damage was done. I wasn't charged because it was a small town and I was a very stupid teenager. Jeff later confessed that I had taken probably twelve inches at least. I didn't have a shit for two days after that.
Years later, I became very popular.....with guys :)
1 year ago
